(US9055749) The invention relates to novel arylpyrroline compounds of formula (I) which have excellent insecticidal activity and which can thus be used as an insecticide.
(US9055749) The invention claimed is: 1. A arylpyrroline compound of formula (I) wherein Q stands for a 2-pyridyl group, a 3-pyridyl group, or a 4-pyridyl group, each group may be substituted with at least one substituent X or X1; X and X1 each independently stand for fluorine, chlorine, bromine, iodine, C1-12haloalkyl, nitro, C1-12alkyl, or C1-12alkoxyl, cyano, C1-12haloalkoxyl, C1-12alkylsulfenyl, C1-12alkylsulfinyl, C1-12alkylsulfonyl, C1-12haloalkylsulfenyl, C1-12haloalkylsulfinyl, or C1-12haloalkylsulfonyl, hydroxyl, thiol, amino, C1-12acylamino, C1-12alkoxy-carbonylamiho, C1-12haloalkoxycarbonylamino, C1-12alkoxyimino, C1-12haloalkoxyimino, or C1-12alkylsulfonylamino, or sulfur pentafluoride; A1, A2, A3 and A4 each independently stand for a carbon atom which may be substituted by a substituent Y, and whereas two adjacent substituents Y together with the carbon atoms to which they are attached may form a 5- or 6-membered aromatic ring, or A1A2A3and A4each independently stand for a nitrogen atom, under the proviso that only 2 of the chemical groups A1, A2, A3 and A4 stand at the same time for nitrogen; Y stands for fluorine, chlorine, bromine, iodine, C1-12haloalkyl, nitro, C1-12alkyl, C3-8cycloalkyl, C3-8cyclohaloalkyl, C1-12alkoxyl, cyano, C1-12haloalkoxyl, C1-12alkylsulfenyl, C1-12alkylsulfinyl, C1-12alkylsulfonyl, C1-12haloalkylsulfenyl, C1-12haloalkylsulfinyl, C1-12haloalkylsulfonyl, C1-12alkylsulfonyloxy, C1-12haloalkylsulfonyloxy, C1-12alkylaminosulfonyl, C1-12haloalkylaminosulfonyl, di(C1-12)alkylaminosulfonyl, or di((C1-12)haloalkyl)aminosulfonyl, hydroxyl, thiol, amino, C1-12alkylamino, di(C1-12)alkylamino, C1-12acylamino, C1-12alkoxycarbonylamino, C1-12haloalkoxycarbonylamino, C1-12alkylsulfonylamino, C1-12haloalkylsulfonylamino, C1-12trialkylsilyl, C1-12alkoxyimino, C1-12haloalkoxyimino, C1-12alkoxyiminoalkyl, C1-12haloalkoxyimino(C1-12)alkyl, C1-12alkylsulfinylimino, C1-12alkylsulfinylimino(C1-12)alkyl, C1-12alkylsulfinylimino(C1-12)alkylcarbonyl, C1-12alkylsulfoxyimino, C1-12alkylsulfoxyimino(C1-12)alkyl, C1-12alkoxycarbonyl, C1-12alkylcarbonyl, aminocarbonyl, C1-12alkylaminocarbonyl, aminothiocarbonyl, C1-12alkylaminothiocarbonyl, di(C1-12)alkylaminocarbonyl, or di(C1-12)alkylaminothiocarbonyl; G stands for a heterocyclic group G1 to G9 having the following formula which may be substituted by a substituent Z which is selected from the group consisting of fluorine, chlorine, bromine, iodine, C1-6 haloalkyl, nitro, C1-6alkoxy, cyano, C1-6haloalkoxy, C1-6alkylsulfenyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6haloalkylsulfenyl, C1-6haloalkylsulfinyl, C1-6haloalkylsulfonyl, hydroxyl and thiol, or represents a chemical group G10 characterized by the following formula: wherein R1 and R2 each independently stand for hydrogen, C1-12alkyl, C3-8cycloalkyl, C1-12haloalkyl, C3-8cyclohaloalkyl, C2-12alkenyl, C2-12alkynyl, C2-12haloalkenyl, cyano, C1-12alkoxycarbonyl, or C1-12, alkoxythiocarbonyl, or R1and R2, together with the carbon atom to which they are attached, form a 3 to 6-membered carbocyclic ring; R3 represents hydrogen, amino, hydroxyl, C1-12alkoxy, C1-12alkylcarbonylamino, C1-12alkylimino, C1-12alkyl, C3-8cycloalkyl, C1-12haloalkyl, cyano, C2-12alkenyl, C2-12alkynyl, or C1-12alkylcarbonyl, or is selected from the group consisting of CH2 -- R5,C(.dbd.O)R5, C(.dbd.S)R5, R4 represents a chemical group selected from the group consisting of hydrogen, cyano, carbonyl, thiocarbonyl, C1-12alkylcarbonyl, C1-12alkylthiocarbonyl, C1-12haloalkylcarbony , C1-12haloalkylthiocarbonyl, C1-12 alkylaminocarbonyl, C1-12alkylaminothiocarbonyl, di(C1-12)alkylaminocarbonyl, di(C1-12)alkylanrinothiocarbonyl, C1-12alkoxyaminocarbonyl, C1-12alkoxyaminothiocarbonyl, C1-12alkoxycarbonyl, C1-12alkoxythiocarbonyl, C1-12thioalkoxycarbonyl, C1-12thioalkoxythiocarbonyl, C1-12alkylsulfonyl, C1-12haloalkylsulfonyl, C3-8cycloalkylcarbonyl, C2-12alkenylcarbonyl, C2-12alkynylcarbonyl, C3-8cycloalkyl-(C1-12)alkylcarbonyl, C1-12alkylsulfenyl(C1-12)alkylcarbonyl, C1-12alkylsulfinyl(C1-12)alkylcarbonyl, C1-12alkylsulfonyl(C1-12)alkylcarbonyl, C1-12alkylcarbonyl(C1-12)alkylcarbonyl, C3-8cyclalkylaminocarbonyl, C2-12alkenylaminocarbonyl, C2-12alkynylaminocarbonyl, and C1-12alkoxy(C1-12)alkyl, or is selected from the group consisting of C(.dbd.O)R5and C(.dbd.S)R5, or R3 and R4, together with the nitrogen atom to which they are bound, form a 3- to 6-membered heterocyclic ring which may be substituted with a substituent X or X1, or may be substituted with a keto, thioketo or nitroimino group; and R5 represents optionally substituted phenyl, or an optionally substituted heterocyclic ring. 2. The arylprroline compound of claim 1, wherein in formula (I) the grouping stands for a grouping P1 to P4 wherein Y is as defined in claim, and k stands for 0, 1, 2, 3 or 4. 3. A composition comprising at least one compound of claim 1 for controlling animal pests. 4. A method for controlling animal pests comprising applying at least one compound of claim 1 to animal pests, their habitat, or both. 5. A method for treating a seed against insects comprising applying at least one compound of claim 1 to the seed. 6. The method of claim 5, wherein the seed is a seed of a conventional plant. 7. The method of claim 5, wherein the seed is a seed of a transgenic plant. 8. The compound of claim 1, wherein the G stands for any one of G1 to G9 as defined in claim 1.
(US9055749) LEGAL DETAILS FOR US2014024680 Actual or expected expiration date=2030-05-18 Legal state=ALIVE Status=GRANTED Event publication date=2013-01-09 Event code=US/APP Event indicator=Pos Event type=Examination events Application details Application country=US US13737536 Application date=2013-01-09 Standardized application number=2013US-13737536 Event publication date=2013-01-09 Event code=US/EXMR Event type=Administrative notifications USPTO Examiner Name Primary Examiner: SHTERENGARTS, SAMANTHA L Event publication date=2013-01-09 Event code=US/ART Event type=Administrative notifications USPTO Art Group ART=1626 Event publication date=2013-01-09 Event code=US/ENT Event type=Administrative notifications Entity Status Set to Undiscounted Business Entity Status: UNDISCOUNTED Event publication date=2013-01-09 Event code=US/AIA Event type=Administrative notifications First Inventor File Indicated: AIA=No Event publication date=2013-01-09 Event code=US/DK Event type=Examination events Attorney Docket Number Docket Nbr: 2923343-355001 Event publication date=2013-01-09 Event code=US/CUST Event type=Examination events Attorney/Agent Customer Number Customer Nbr: 84331 Event publication date=2013-02-13 Event code=US/INCD Event type=Examination events Event type=OAO Notice Mailed--Application Incomplete--Filing Date Assigned Event publication date=2013-02-13 Event code=US/APPFILEREC Event type=Administrative notifications Event type=OAO Filing Receipt Event publication date=2013-06-13 Event code=US/FPAFF Event type=Payment or non-payment notifications Payment of additional filing fee/Preexam Event publication date=2013-10-17 Event code=US/RECEIPTUP Event type=Administrative notifications Event type=OAO Filing Receipt - 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